79-17-4

Basic information

• Product Name: pimagedine
• Synonyms: pimagedine;Aminoguanidine mordant;1-Aminoguanidine;Aminate base;Amino(imino)methylhydrazine;N-Aminoguanidine;Aids030897;Aids-030897
• CAS NO: 79-17-4
• Molecular Formula: CH₆N₄
• Molecular Weight: 74.11
• EINECS: 201-183-1
• Product Categories: Pharmaceutical Intermediates
• Mol File: 79-17-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 182-185 °C (decomp)
• Boiling Point: 261.4oC at 760 mmHg
• Flash Point: 111.9oC
• Appearance: /
• Density: 1.72g/cm3
• Vapor Pressure: 0.0116mmHg at 25°C
• Refractive Index: 1.6660 (estimate)
• PKA: 11.08±0.70(Predicted)
• CAS DataBase Reference: pimagedine(CAS DataBase Reference)
• NIST Chemistry Reference: pimagedine(79-17-4)
• EPA Substance Registry System: pimagedine(79-17-4)

Safety Data

• Hazardous Substances Data: 79-17-4(Hazardous Substances Data)

Usage

Definition

ChEBI: A one-carbon compound whose unique structure renders it capable of acting as a derivative of hydrazine, guanidine or formamide.

Enzyme inhibitor

This substituted hydrazine (FWhydrochloride = 110.55 g/mol; CAS 79-17-4), also named pimagedine, is a strong inhibitor of diamine oxidases as well as nitric oxide synthase. Note that aminoguanidine also inhibits the formation of advanced glycosylation end-products, reportedly by reacting with and trapping Amadori rearrangement-derived fragmentation products in solution. In view of this property, aminoguanidine has often been used to treat complications associated with chronic diabetes. Target(s): amine oxidase (copper-containing), or diamine oxidase; methylamine dehydrogenase; tryptophan tryptophylquinone enzymes; nitric-oxide synthase; b-fructofuranosidase, or invertase; monoamine oxidase, or amine oxidase; histidine decarboxylase; aldose reductase; catalase; formation of advanced glycosylation end products; adenosylmethionine decarboxylase; arginine deaminase; arginine kinase; aspartate aminotransferase; histamine N-methyltransferase.

InChI:InChI=1/CH6N4/c2-1(3)5-4/h4H2,(H4,2,3,5)

Upstream product

• 674-81-7 nitrosoguanidine 
• 14527-26-5 2-methylisothiourea sulphate 
• 4362-82-7 Pinakolon-guanylhydrazon 
• 4362-88-3 2-(1-methylethylidene)hydrazinecarboximidamide 
• 556-88-7 nitroguanidine 
• 7732-18-5 water 
• 556-88-7 2-nitroguanidine 
• 35600-34-1 S-methyl isothiosemicarbazide hydroiodide 
• 1937-19-5 1-aminoguanidine hydrochloride 
• 420-04-2 CYANAMID 
• 302-01-2 hydrazine 
• 2582-30-1 aminoguanidine bicarbonate 
• 7803-57-8 hydrazine hydrate 
• 64-19-7 acetic acid 

Downstream Products

• 5373-68-2 5-amino-4-phenyl-2,4-dihydro-[1,2,4]triazolidine-3-thione 
• 86044-63-5 vanillylidenamino-guanidine 
• 6237-77-0 Glyoxylsaeure-guanylhydrazon 
• 5382-85-4 trans-cinnamylidenamino-guanidine 
• 27277-03-8 5-amino-3-hydroxymethyl-1H-1,2,4-triazole 
• 113038-69-0 2,2'-butanediyldioxy-di-benzaldehyde bis-carbamimidoylhydrazone 
• 118837-11-9 3,3'-dimethoxy-4,4'-pentanediyldioxy-di-benzaldehyde bis-carbamimidoylhydrazone 
• 122856-95-5 (4-nitro-benzenesulfonylamino)-guanidine 
• 122881-74-7 [(N-acetyl-sulfanilyl)-amino]-guanidine 
• 6578-46-7 N-(α-Cyan-benzyliden)-N'-diaminomethylen-hydrazin 
• 93651-23-1 1--3-phenyl-harnstoff 
• 29030-02-2 (3-benzoyl-thioureido)-guanidine 
• 63472-01-5 C₁₉H₂₂N₄O₂*ClH 
• 104667-76-7 N-(5-Amino-4H-[1,2,4]triazol-3-yl)-4-chloro-benzenesulfonamide 

Relevant articles and documents

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Microscale Parallel Synthesis of Acylated Aminotriazoles Enabling the Development of Factor XIIa and Thrombin Inhibitors

Herein we report a microscale parallel synthetic approach allowing for rapid access to libraries of N-acylated aminotriazoles and screening of their inhibitory activity against factor XIIa (FXIIa) and thrombin, which are targets for antithrombotic drugs. This approach, in combination with post-screening structure optimization, yielded a potent 7 nM inhibitor of FXIIa and a 25 nM thrombin inhibitor; both compounds showed no inhibition of the other tested serine proteases. Selected N-acylated aminotriazoles exhibited anticoagulant properties in vitro influencing the intrinsic blood coagulation pathway, but not extrinsic coagulation. Mechanistic studies of FXIIa inhibition suggested that synthesized N-acylated aminotriazoles are covalent inhibitors of FXIIa. These synthesized compounds may serve as a promising starting point for the development of novel antithrombotic drugs.

Glycation Cross-link Breakers to Increase Resistance to Enzymatic Degradation

The present invention relates to a method to treat a grafts, implant, scaffold, and constructs, including allografts, xenografts, autografts, and prosthetics comprising collagen, with an inhibitor of collagen cross-links and/or advanced glycation endproducts (AGE), in order to alleviate the mechanical weakness induced by the cross-links The invention also provides for kits for use in the operating theater during autograft, allograft or xenograft procedures, or for preparing allograft, xenografts or prosthetics that have not been already treated prior to packaging. The kit comprises a first agent or agents that inhibit collagen cross-links and/or advanced glycation endproducts, instructions for use, optionally a wash or rinse agent, and a device for containing the graft and first agent.